Top-rated asphalt shingle roofing installers and replacers.

Get matched with top asphalt shingle roofing installers and replacers in Chestertown, MD

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Asphalt shingle roofing installers and replacers in Chestertown

TDS Contractors

420 Jarman Avenue
New on HomeAdvisorNew on HomeAdvisor
Approved Pro

TDS Contractors

420 Jarman Avenue
New on HomeAdvisorNew on HomeAdvisor
Approved Pro
7 years of experience
Free onsite estimate

At TDS Contractors, our company is based on the belief that our customers' needs are of the utmost importance. Our team is committed to meeting those needs. We welcome the opportunity to earn your trust and deliver you the best service. No job is too big or too small for our experienced team. Call today for a quote.

At TDS Contractors, our company is based on the belief that our customers' needs are of the utmost importance. Our team is committed to meeting those needs. We welcome the opportunity to earn your trust and deliver you the best service. No job is too big or too small for our experienced team. Call today for a quote.


Avatar for Recinos Siding Contractor, LLC

Recinos Siding Contractor, LLC

806 Shore Dr Edgewater Md
New on HomeAdvisorNew on HomeAdvisor
Approved Pro

Recinos Siding Contractor, LLC

806 Shore Dr Edgewater Md
New on HomeAdvisorNew on HomeAdvisor
Approved Pro
30 years of experience
Free onsite estimate

We are a locally owned and operated company. We value honesty and integrity in all aspects of our business. We offer a variety of home improvement services that are customized to each individual project. We pride ourselves on the quality of our work, as well as our commitment to outstanding results. We look forward to building lasting relationships with our clients and guarantee your satisfaction!

We are a locally owned and operated company. We value honesty and integrity in all aspects of our business. We offer a variety of home improvement services that are customized to each individual project. We pride ourselves on the quality of our work, as well as our commitment to outstanding results. We look forward to building lasting relationships with our clients and guarantee your satisfaction!


Avatar for Home Genius Exteriors

Home Genius Exteriors

8201 Corporate Drive, Suite G10
4.94(
354
)
Approved Pro

Home Genius Exteriors

8201 Corporate Drive, Suite G10
4.94(
354
)
Approved Pro
Super Service Award
Customers say: Super punctual
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
32 local quotes requested

Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

"Just imaging solution"

Jack S on April 2025

Elevate your home with Home Genius Exteriors, setting the standard in Maryland and Washington DC by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It’s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

"Just imaging solution"

Jack S on April 2025


Avatar for Power Home Remodeling

Power Home Remodeling

2501 Seaport Drive
4.51(
341
)
Approved Pro

Power Home Remodeling

2501 Seaport Drive
4.51(
341
)
Approved Pro
Customers say: Super punctual
2632 local quotes requested
33 years of experience

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"Their roofing crew stole my deer skull from the front of my house and it magically reappeared next to their van on the street after threatening to call the police. While stripping off the old roofing, they let the debris build up on my front bushes causing unrepairable damage. Unless you can speak Spanish you won't be able to communicate with their laborors and there is no boss working with them on site to help bridge the language barrier. They left scraps from their lunch around my front yard, avacado skins and shrimp tails and also cigarette butts, one of them smoked the whole time. The trim and gutters crews were fine but the cleanup after they were all done could have been better they left a decent amount of roofing nails and gutter screws even in plain sight in my driveway. Also had a couple of scheduling issues with material availability the attic insulation installers causing the project to be completed more than a week late. "

Brian D on August 2025

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"Their roofing crew stole my deer skull from the front of my house and it magically reappeared next to their van on the street after threatening to call the police. While stripping off the old roofing, they let the debris build up on my front bushes causing unrepairable damage. Unless you can speak Spanish you won't be able to communicate with their laborors and there is no boss working with them on site to help bridge the language barrier. They left scraps from their lunch around my front yard, avacado skins and shrimp tails and also cigarette butts, one of them smoked the whole time. The trim and gutters crews were fine but the cleanup after they were all done could have been better they left a decent amount of roofing nails and gutter screws even in plain sight in my driveway. Also had a couple of scheduling issues with material availability the attic insulation installers causing the project to be completed more than a week late. "

Brian D on August 2025


Avatar for Riptide Remodeling LLC

Riptide Remodeling LLC

605 Main Street, Unit 101
5.00(
17
)
Approved Pro

Riptide Remodeling LLC

605 Main Street, Unit 101
5.00(
17
)
Approved Pro
47 local quotes requested
15 years of experience

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction, from the start to the completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"From Sales to installation of my tub-shower conversion very professional. job well done. One issue I think was my fault there is no place to set a bar of soap of shampoo. I assumed that no installation product comes with such a place. Not so; so don't forget to ask and/or request. I still would recommend Riptide for sure."

GLENN R on May 2025

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction, from the start to the completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"From Sales to installation of my tub-shower conversion very professional. job well done. One issue I think was my fault there is no place to set a bar of soap of shampoo. I assumed that no installation product comes with such a place. Not so; so don't forget to ask and/or request. I still would recommend Riptide for sure."

GLENN R on May 2025


Avatar for Roofing Pups, Roofing & Siding

Roofing Pups, Roofing & Siding

633 Keith Lane
4.94(
33
)
Approved Pro

Roofing Pups, Roofing & Siding

633 Keith Lane
4.94(
33
)
Approved Pro
Super Service Award
Customers say: True professional
882 local quotes requested
31 years of experience

Since 1994, Air Tite Exteriors has provided homeowners in Maryland and D.C with top quality, factory-direct products, professionally installed by factory trained installers. Locally-owned. GAF Master Elite roofing certification.

"Great customer service, quick, high-quality work. I appreciated the thorough cleanup before leaving the job site."

Darcy H on September 2025

Since 1994, Air Tite Exteriors has provided homeowners in Maryland and D.C with top quality, factory-direct products, professionally installed by factory trained installers. Locally-owned. GAF Master Elite roofing certification.

"Great customer service, quick, high-quality work. I appreciated the thorough cleanup before leaving the job site."

Darcy H on September 2025


Avatar for Complete Exteriors, LLC

Complete Exteriors, LLC

6102 Cool Spring Terrace South
4.68(
64
)
Approved Pro

Complete Exteriors, LLC

6102 Cool Spring Terrace South
4.68(
64
)
Approved Pro
Customers say: True professional
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
52 local quotes requested

Here at Complete Exteriors we are driven by two things. Offering a complete and professional job completion, and doing what we say we will. We know what the frustrations are of the homeowner, When we tell you we will meet you at a time and date, we will be there! When we say we will complete the job on a certain date, we will! You shouldn’t hope to have a professional job done by a contractor - you should expect it!

"We had our roof replaced. Communication was very clear as to price, options and timing. The job was done on time and to full satisfaction. We would hire this firm again without hesitation."

Shawn K on September 2025

Here at Complete Exteriors we are driven by two things. Offering a complete and professional job completion, and doing what we say we will. We know what the frustrations are of the homeowner, When we tell you we will meet you at a time and date, we will be there! When we say we will complete the job on a certain date, we will! You shouldn’t hope to have a professional job done by a contractor - you should expect it!

"We had our roof replaced. Communication was very clear as to price, options and timing. The job was done on time and to full satisfaction. We would hire this firm again without hesitation."

Shawn K on September 2025


Avatar for AJB Contractors LLC

AJB Contractors LLC

6519 Cleveland Ave
5.00(
5
)
Approved Pro

AJB Contractors LLC

6519 Cleveland Ave
5.00(
5
)
Approved Pro
Free onsite estimate

We invite you to experience a tradition of customer satisfaction that will exceed your greatest expectations. Our professionalism and quality workmanship will accurately reflect your taste and lifestyle. From conception to completion, we work with you until the job is done. We are ethical, honest, and easy to communicate with. Call us today you'll be pleased you did. Thank you

We invite you to experience a tradition of customer satisfaction that will exceed your greatest expectations. Our professionalism and quality workmanship will accurately reflect your taste and lifestyle. From conception to completion, we work with you until the job is done. We are ethical, honest, and easy to communicate with. Call us today you'll be pleased you did. Thank you


Avatar for Tar Heel Construction Group, LLC

Tar Heel Construction Group, LLC

1212 East Churchville Road, Suite 101
4.96(
69
)
Approved Pro

Tar Heel Construction Group, LLC

1212 East Churchville Road, Suite 101
4.96(
69
)
Approved Pro
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
19 local quotes requested

As a roofing company serving Bel Air, Maryland since 2004 our goal is simple. We will exceed our customers' roofing expectations with quality roofing work and craftsmanship every time. By building relationships, through the home improvement process, customers' are given a home to be proud of, a roofing company that they trust, and the peace of mind knowing that we stand behind 100% of our work 100% of the time. Since its conception Tar Heel Construction Group, LLC has focused on three core business principles: accountability, roofing job quality, and customer satisfaction. Click here to view our roofing service locations in the Greater Baltimore region!

"Courteous and professional recent roof and gutter replacement. Thorough presentation of product by Brian, hard working crew, and good supervision of task from beginning to completion by Ryan and Brian. Attention given to each of my questions and concerns. Good phone communication for time schedules, arrivals, changes, etc."

Karen T on April 2020

As a roofing company serving Bel Air, Maryland since 2004 our goal is simple. We will exceed our customers' roofing expectations with quality roofing work and craftsmanship every time. By building relationships, through the home improvement process, customers' are given a home to be proud of, a roofing company that they trust, and the peace of mind knowing that we stand behind 100% of our work 100% of the time. Since its conception Tar Heel Construction Group, LLC has focused on three core business principles: accountability, roofing job quality, and customer satisfaction. Click here to view our roofing service locations in the Greater Baltimore region!

"Courteous and professional recent roof and gutter replacement. Thorough presentation of product by Brian, hard working crew, and good supervision of task from beginning to completion by Ryan and Brian. Attention given to each of my questions and concerns. Good phone communication for time schedules, arrivals, changes, etc."

Karen T on April 2020


AML Top Quality Construction

105 Port Court
4.83(
21
)
Approved Pro

AML Top Quality Construction

105 Port Court
4.83(
21
)
Approved Pro
Customers say: Quick response
16 years of experience
Free onsite estimate

AML Top Quality Construction is a locally owned and operated company, serving the Grasonville, MD area and surrounding communities. We will help you create that indoor living space you have always dreamed of! From your kitchen, to your bathroom, or your basement, we can upgrade or give you that dream space. We offer professional craftsmanship, reasonable rates, and friendly customer service. Call us now!

"We are very pleased with the quality of work and the professionalism of Casey and the AML crew. The work was completed in the timeframe we requested and within the price range we expected. Casey was extremely responsive to emails and text messages and adaptable to change requests. The crew was very respectful and accommodating in their work schedule and did a great job keeping the construction area safe and clean. We were very pleased and plan to use them again for future projects."

Larry F on September 2025

AML Top Quality Construction is a locally owned and operated company, serving the Grasonville, MD area and surrounding communities. We will help you create that indoor living space you have always dreamed of! From your kitchen, to your bathroom, or your basement, we can upgrade or give you that dream space. We offer professional craftsmanship, reasonable rates, and friendly customer service. Call us now!

"We are very pleased with the quality of work and the professionalism of Casey and the AML crew. The work was completed in the timeframe we requested and within the price range we expected. Casey was extremely responsive to emails and text messages and adaptable to change requests. The crew was very respectful and accommodating in their work schedule and did a great job keeping the construction area safe and clean. We were very pleased and plan to use them again for future projects."

Larry F on September 2025

...
Showing 1-10 of 207
FAQs for asphalt shingle roofing installation and replacement projects in Chestertown, MD

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Chestertown, MD homeowners’ guide to asphalt shingle roofing installations and replacements

From average costs to expert advice, get all the answers you need to get your job done.

  • A farmhouse in Autumn

    Discover how much roof replacement costs in Michigan based on the price of materials, labor, permits, and inspections with our comprehensive cost guide.

  • Roofing contractor replacing the old shingles

    Discover how roof pitch, shape, labor, and materials influence roof replacement costs with our guide to roof replacement costs in New Jersey.

  • Two workers replacing broken tiles

    HomeAdvisor's Texas roof replacement guide explores how much it costs to replace a roof in Texas. Find out how much you'll spend to replace your roof by type, pitch, and location.

  • roof view of residential home in California

    HomeAdvisor’s California Roof Cost Guide covers the cost of a new roof in California, based on the city, roof size, and material. Use our guide to estimate your roof replacement cost in California.

  • roof view of residential home in florida

    HomeAdvisor’s Florida Roof Cost Guide covers the average roof replacement cost in Florida, based on the city, roof size, and material. Use our guide to estimate your Florida roof replacement cost

  • asphalt shingle roof on house

    Explore shingle roof replacement costs and how key factors like roof size, shingle type, and labor impact the total cost of your roofing project.